IE60756B1 - Improved chelator for anaerobic sealants - Google Patents

Improved chelator for anaerobic sealants

Info

Publication number: IE60756B1
Authority: IE; Ireland
Prior art keywords: hrs; cure; kgn; chelator; hedta
Prior art date: 1987-03-12

Application number

IE64387A

Other languages

English (en)

Other versions

IE870643L (en

Original Assignee

Loctite Ireland Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-03-12

Filing date

1987-03-12

Publication date

1994-08-10

1987-03-12 Application filed by Loctite Ireland Ltd filed Critical Loctite Ireland Ltd

1987-03-12 Priority to IE64387A priority Critical patent/IE60756B1/en

1988-03-10 Priority to EP19880302068 priority patent/EP0282292B1/fr

1988-03-10 Priority to JP5730988A priority patent/JPS63243189A/ja

1988-03-10 Priority to DE8888302068T priority patent/DE3870491D1/de

1988-09-12 Publication of IE870643L publication Critical patent/IE870643L/xx

1994-08-10 Publication of IE60756B1 publication Critical patent/IE60756B1/en

Links

239000002738 chelating agent Substances 0.000 title claims abstract description 40
239000000565 sealant Substances 0.000 title claims abstract description 24
URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 claims abstract description 33
239000000203 mixture Substances 0.000 claims abstract description 31
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims abstract description 8
238000009472 formulation Methods 0.000 abstract description 16
238000012360 testing method Methods 0.000 abstract description 14
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 12
229910052802 copper Inorganic materials 0.000 abstract description 12
239000010949 copper Substances 0.000 abstract description 12
-1 acrylate ester Chemical class 0.000 abstract description 9
238000011109 contamination Methods 0.000 abstract description 4
239000000853 adhesive Substances 0.000 abstract description 3
230000001070 adhesive effect Effects 0.000 abstract description 3
229910021645 metal ion Inorganic materials 0.000 abstract description 3
UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 abstract description 2
230000000052 comparative effect Effects 0.000 abstract 1
239000011734 sodium Substances 0.000 description 16
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 12
239000000243 solution Substances 0.000 description 9
150000002148 esters Chemical class 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000000178 monomer Substances 0.000 description 4
LQPLDXQVILYOOL-UHFFFAOYSA-I pentasodium;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O LQPLDXQVILYOOL-UHFFFAOYSA-I 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000000047 product Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000006228 supernatant Substances 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
229920000058 polyacrylate Polymers 0.000 description 3
230000002028 premature Effects 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 2
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 2
230000032683 aging Effects 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
229940081974 saccharin Drugs 0.000 description 2
235000019204 saccharin Nutrition 0.000 description 2
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 2
BSRKJFGTFRITNT-AYFQBXJRSA-N (7E)-5,8-diethyl-7-hydroxyiminododecan-6-ol 2-[4-[(Z)-hydroxyiminomethyl]phenyl]-5-nonylphenol Chemical compound CCCCC(CC)C(O)C(=N\O)\C(CC)CCCC.CCCCCCCCCc1ccc(c(O)c1)-c1ccc(\C=N/O)cc1 BSRKJFGTFRITNT-AYFQBXJRSA-N 0.000 description 1
GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 description 1
JFZBUNLOTDDXNY-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)propoxy]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)OCC(C)OC(=O)C(C)=C JFZBUNLOTDDXNY-UHFFFAOYSA-N 0.000 description 1
RIYDSTPQZDWTBD-UHFFFAOYSA-N 2-[2-[2-[2-(2-chloroprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-chloroprop-2-enoate Chemical compound ClC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(Cl)=C RIYDSTPQZDWTBD-UHFFFAOYSA-N 0.000 description 1
LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
XNCSCQSQSGDGES-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]propyl-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)C(C)CN(CC(O)=O)CC(O)=O XNCSCQSQSGDGES-UHFFFAOYSA-N 0.000 description 1
AEPWOCLBLLCOGZ-UHFFFAOYSA-N 2-cyanoethyl prop-2-enoate Chemical compound C=CC(=O)OCCC#N AEPWOCLBLLCOGZ-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
FCKYPQBAHLOOJQ-UHFFFAOYSA-N Cyclohexane-1,2-diaminetetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)C1CCCCC1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000013522 chelant Substances 0.000 description 1
230000009920 chelation Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229940079895 copper edta Drugs 0.000 description 1
OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
229960003330 pentetic acid Drugs 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2003/1034—Materials or components characterised by specific properties
- C09K2003/1065—Anaerobically hardenable materials
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/04—Non-macromolecular organic compounds
- C09K2200/0458—Nitrogen-containing compounds
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0625—Polyacrylic esters or derivatives thereof

Landscapes

Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Adhesives Or Adhesive Processes (AREA)
Sealing Material Composition (AREA)

IE64387A 1987-03-12 1987-03-12 Improved chelator for anaerobic sealants IE60756B1 (en)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
IE64387A IE60756B1 (en)	1987-03-12	1987-03-12	Improved chelator for anaerobic sealants
EP19880302068 EP0282292B1 (fr)	1987-03-12	1988-03-10	Chelatant pour agents d'étanchéité anaérobies
JP5730988A JPS63243189A (ja)	1987-03-12	1988-03-10	嫌気シーラント組成物
DE8888302068T DE3870491D1 (de)	1987-03-12	1988-03-10	Chelatierungsmittel fuer anaerobe dichtungsmaterialien.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IE64387A IE60756B1 (en)	1987-03-12	1987-03-12	Improved chelator for anaerobic sealants

Publications (2)

Publication Number	Publication Date
IE870643L IE870643L (en)	1988-09-12
IE60756B1 true IE60756B1 (en)	1994-08-10

Family

ID=11016084

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE64387A IE60756B1 (en)	1987-03-12	1987-03-12	Improved chelator for anaerobic sealants

Country Status (4)

Country	Link
EP (1)	EP0282292B1 (fr)
JP (1)	JPS63243189A (fr)
DE (1)	DE3870491D1 (fr)
IE (1)	IE60756B1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9506294D0 (en) *	1995-03-28	1995-05-17	Switched Reluctance Drives Ltd	Improvements in switched reluctance machines
GB2538498B (en)	2015-05-15	2017-12-20	Henkel IP & Holding GmbH	Anaerobically curable (meth) acrylate compositions characterised by stabilisers with at least one glycinate group
GB202405270D0 (en)	2024-04-12	2024-05-29	Henkel Ag & Co Kgaa	Anaerobically curable adhesive compositions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL36289A (en) *	1970-03-18	1974-03-14	Loctite Corp	Highly stable anaerobic compositions comprising acrylate ester monomer
US4235986A (en) *	1979-04-02	1980-11-25	National Starch And Chemical Corporation	Anaerobic curing adhesive composition and process for making same

1987
- 1987-03-12 IE IE64387A patent/IE60756B1/en not_active IP Right Cessation
1988
- 1988-03-10 DE DE8888302068T patent/DE3870491D1/de not_active Expired - Fee Related
- 1988-03-10 EP EP19880302068 patent/EP0282292B1/fr not_active Expired
- 1988-03-10 JP JP5730988A patent/JPS63243189A/ja active Pending

Also Published As

Publication number	Publication date
EP0282292A2 (fr)	1988-09-14
EP0282292A3 (en)	1990-03-14
EP0282292B1 (fr)	1992-04-29
DE3870491D1 (de)	1992-06-04
IE870643L (en)	1988-09-12
JPS63243189A (ja)	1988-10-11

Legal Events

Date	Code	Title	Description
1996-03-20	MM4A	Patent lapsed
1997-02-12	MM4A	Patent lapsed	Free format text: "ERRATUM: ADVERTISED OM JOURNAL NO.1782 OF 20/3/96, PAGE 135"
2004-04-07	MM4A	Patent lapsed

Publication	Publication Date	Title
JP3511144B2 (ja)	2004-03-29	促進剤系の貯蔵安定性溶液
US4350535A (en)	1982-09-21	Water-dispersible paste composition of metal powder
US3682875A (en)	1972-08-08	Stabilized anaerobic sealant composition
CA2171453A1 (fr)	1995-03-30	Analogues du glutathion et panels renfermant des mimetiques du glutathion
US4235986A (en)	1980-11-25	Anaerobic curing adhesive composition and process for making same
JPS61296072A (ja)	1986-12-26	安定化された金属顔料
WO1997002328A1 (fr)	1997-01-23	Nouvel adhesif dentaire
US4038475A (en)	1977-07-26	Highly stable anaerobic compositions
IE60756B1 (en)	1994-08-10	Improved chelator for anaerobic sealants
US3294775A (en)	1966-12-27	Reaction products of stabilized rosin amine and organic acid phosphate esters
EP0429180A3 (en)	1991-11-06	Non-toxic corrosion inhibitive compositions and method for inhibiting corrosion
US4262106A (en)	1981-04-14	Highly stable anaerobic compositions and process for preparing them
DE3376748D1 (en)	1988-06-30	Process for the preparation of compounds containing (meth)acrylic-acid esters, (meth)acrylic-acid esters and anaerobically curable adhesives and putty-like masses
CA1130031A (fr)	1982-08-17	Substances acryliques de type anaerobies, stabilisees contre la degradation par les acides
DE2543597C2 (de)	1982-04-22	Ungesättigte titandioxidhaltige Polyesterharzmassen
CA3077392C (fr)	2025-02-11	Accélérateurs de durcissement pour compositions durcissables par voie anaérobie
US4460760A (en)	1984-07-17	Anaerobically curable compositions
US4055542A (en)	1977-10-25	Anaerobically curable sealing composition containing (A) acrylate derivative of bisphenol A and (B) hydroxyacrylate
AU626321B2 (en)	1992-07-30	Process for preparing sulfur solvent compositions
KR20010079886A (ko)	2001-08-22	알루미늄 기재를 실 형성을 위해 혐기성 실란트로결합하는 방법
US4429063A (en)	1984-01-31	Anaerobically curable sealant and adhesive composition
JPH068407B2 (ja)	1994-02-02	接着性に優れた嫌気性接着剤
SU697545A1 (ru)	1979-11-15	Клей
KR102064959B1 (ko)	2020-01-10	비산먼지 발생 방지 조성물
DE2005043C3 (de)	1981-06-04	Verfahren zur Herstellung von anaerob polymerisierbaren flüssigen Mischungen mit erhöhter Härtungsgeschwindigkeit